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CAS No.: | 4291-63-8 |
---|---|
Name: | Cladribine |
Article Data: | 38 |
Molecular Structure: | |
Formula: | C10H12ClN5O3 |
Molecular Weight: | 285.69 |
Synonyms: | 2-Chloro-2-deoxy-beta-adenosine;2-Chloro-6-amino-9-(2-deoxy-beta-D-erythropentofuranosyl)purine;Chlorodeoxyadenosine;RWJ 26251;Adenosine,2-chloro-2'-deoxy-;Leustatin;24757-90-2;2-CdA;2-Chlorodeoxyadenosine;Adenosine, 2-chloro-2-deoxy;Cladribine(Base);Cadribine;Leustatin (TN);Cladribine [USAN:BAN:INN];2-Chloro-2-deoxyadenosine; |
EINECS: | 224-427-9 |
Density: | 1.402 g/cm3 |
Melting Point: | 181-185 °C(lit.) |
Boiling Point: | 387.1 °C at 760 mmHg |
Flash Point: | 187.9 °C |
Appearance: | White Crystalline Solid |
Hazard Symbols: | T |
Risk Codes: | 36/37/38-23/24/25 |
Safety: | 26-45-36-22 |
PSA: | 119.31000 |
LogP: | 0.28380 |
2-chloro-2'-deoxyadenosine
Conditions | Yield |
---|---|
With ammonia In methanol at 60℃; for 11h; | 100% |
With ammonia In methanol at 60℃; | 59% |
2-chloro-N6,N6-dibenzoyl-3′,5′-O-dibenzoyl-2′-deoxyadenosine
2-chloro-2'-deoxyadenosine
Conditions | Yield |
---|---|
With ammonia In methanol at 0 - 20℃; for 12h; | 95% |
9-(3,5-di-O-benzoyl-2-deoxy-β-D-erythro-pentofuranosyl)-2,6-dichloropurine
2-chloro-2'-deoxyadenosine
Conditions | Yield |
---|---|
With ammonia In methanol; dichloromethane at 80℃; for 7h; | 94% |
6-amino-2-chloro-9-(2'deoxy-3',5'-di-O-acetyl-β-D-erythro-pentofuranosyl)-9H-purine
2-chloro-2'-deoxyadenosine
Conditions | Yield |
---|---|
With sodium carbonate In methanol at 20℃; for 2h; pH=8 - 9; | 93% |
With ammonia In methanol at 0 - 20℃; | 0.62 g |
2-chloro-6-amino-9-[3,5-di-O-(4-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl]-purine
2-chloro-6-trimethylsilylamino-9-[3,5-di-O-(4-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl]-purine
2-chloro-2'-deoxyadenosine
Conditions | Yield |
---|---|
With sodium methylate In methanol at 20 - 30℃; for 6h; | 90% |
Conditions | Yield |
---|---|
With magnesium hydroxide; purine nucleoside phosphorylase In water at 45℃; | 88% |
9-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-2,6-dichloropurine
2-chloro-2'-deoxyadenosine
Conditions | Yield |
---|---|
With ammonia In methanol; dichloromethane at 80℃; for 7h; | 87% |
2,6-Dichloro-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-purine
2-chloro-2'-deoxyadenosine
Conditions | Yield |
---|---|
With ammonia In methanol at 110℃; for 5h; Sealed tube; | 86% |
With ammonia In methanol at 100℃; for 5h; | 71% |
2-chloro-9-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-6-(2-pentylimidazol-1-yl)purine
2-chloro-2'-deoxyadenosine
Conditions | Yield |
---|---|
With ammonia In methanol at 60℃; for 13h; | 85% |
2-chloro-9-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-6-(2-propylimidazol-1-yl)purine
methanol
A
2-chloro-9-(2'deoxy-β-D-erythro-pentofuranosyl)-6-methoxy-9H-purine
B
2-chloro-2'-deoxyadenosine
Conditions | Yield |
---|---|
With ammonia at 40℃; for 15h; | A 85% B n/a |
1. Introduction of Cladribine
Cladribine (CAS NO.4291-63-8) is a white crystalline solid. Its IUPAC Name is (2R,3S,5R)-5-(6-amino-2-chloropurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol. Its water solubility is 6.35e+00 g/l. The Classification Code is Antineoplastic; Antineoplastic agents; Drug / Therapeutic Agent; Human Data; Immunologic Factors; Immunosuppressive agents; Mutation data; Reproductive Effect. Cladribine belongs to Bases & Related Reagents;Nucleotides;Pharmaceuticals;API. Besides, it should be stored in Freezer.
2. Properties of Cladribine
Physical properties about Cladribine are:
(1)Index of Refraction: 1.87; (2)Molar Refractivity: 63.7 cm3; (3)Molar Volume: 140.1 cm3; (4)Polarizability: 25.25×10-24cm3; (5)Surface Tension: 93.5 dyne/cm; (6)Density: 2.03 g/cm3; (7)Flash Point: 285 °C; (8)Enthalpy of Vaporization: 87.03 kJ/mol; (9)Melting Point: 181-185 °C(lit.); (10)Boiling Point: 547.6 °C at 760 mmHg; (11)Vapour Pressure: 7.95E-13 mmHg at 25°C.
3. Structure Descriptors of Cladribine
(1)Canonical SMILES: C1C(C(OC1N2C=NC3=C2N=C(N=C3N)Cl)CO)O
(2)Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=NC3=C2N=C(N=C3N)Cl)CO)O
(3)InChI: InChI=1S/C10H12ClN5O3/c11-10-14-8(12)7-9(15-10)16(3-13-7)6-1-4(18)5(2-17)19-6/h3-6,17-18H,1-2H2,(H2,12,14,15)/t4-,5+,6+/m0/s1
(4)InChIKey: PTOAARAWEBMLNO-KVQBGUIXSA-N
4. Toxicity of Cladribine
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
man | TDLo | intravenous | 700ug/kg/7D-C (0.7mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | American Journal of Hematology. Vol. 53, Pg. 209, 1996. |
mouse | LD50 | intraperitoneal | 150mg/kg (150mg/kg) | Leukemia and Lymphoma. Vol. 5, Pg. 1, 1991. |